How Will I Make Money Doing That?

How will I make money doing that?

This is the most frequent fear I hear from clients who are contemplating a career change. Worrying about how you will make money while dreaming about your ideal career is like being doused with cold water while sleeping—disruptive at best, completely unnerving at worst. Here are some tips for how to allow yourself to dream about your ideal career AND figure out how you’re going to make money.

Create a Dreaming Sandbox
(The kind kids play in, not the one the cat uses.)
In the Internet world, web developers have what they call a “sandbox.” This is a web-based environment solely for the developer where she can play with new code and see how it works on a pseudo-version of the website, without messing up anything on the real site.

Create your own Dreaming Sandbox where you allow yourself to play with new ideas. Don’t worry if the ideas you’re playing with can make it in the real world or not, just allow them to form and evolve. Have fun with it, let yourself have silly, impractical ideas. Letting yourself have those ideas will lead you down paths you’ve never before explored.

Put Your Fears in the Parking Lot
As you allow yourself to start dreaming, fears will inevitably come up. Write down your fears and put them aside—I call it the “Parking Lot”—to deal with later. This way you aren’t resisting the fears, but you also aren’t letting them get in the way of the creative process.

Solve for Career and Money as Two Separate Problems
Note how you feel when you say the below statements to yourself:

Statement 1
I really want to be a <insert career idea here> but I also need to make <insert amount of money>.

Statement 2
I really want to be a <insert career idea>; what’s the next step to move toward it?
I would like to make <insert amount of money>, how can I do that?

I’m guessing Statement 2 feels better. Perhaps it even blew your mind a bit with new possibilities you hadn’t considered before. When you join the questions “What will I do?” and “How will I make money?” you are requiring your dream to deliver the financial goods right away. This often feels like an insurmountable problem, so we stop dreaming. When you separate these questions, new possibilities unfold. Suddenly there are many ways to move toward your heart’s desire and make money along the way.

The next time someone asks you how you’ll make money pursuing your dream, tell them you’ll do it the same way you always have—with style, creativity, and a little elbow grease.


If you live in Seattle, check out my upcoming Mastering Money workshop.